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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/32703


    Title: 功能性環化胍基衍生物的合成與其在質譜訊號強化之應用
    Other Titles: Synthesis of functional cyclic guanidino derivatives and their application in the signal enhancement of mass spectrometer
    Authors: 謝裕澤;Shieh, Yu-tse
    Contributors: 淡江大學化學學系碩士班
    鄭建中;Cheng, Chien-chung;施增廉;Shih, Tzenge-lien
    Keywords: 微量蛋白質;基質輔助雷射脫附游離法;訊號強化;胍基衍生物;正電荷;Low Abundant Proteins;MALDI;Signal Enhancement;Guanidino Derevitives;Positive Charge
    Date: 2007
    Issue Date: 2010-01-11 02:36:21 (UTC+8)
    Abstract: 微量蛋白質的偵測,在蛋白質體學研究中是非常具挑戰的主題。利用化學法修飾生物分子的帶電性,進而提升質譜訊號的靈敏度,則是目前具有潛力的解決方法之ㄧ。其中以胍基衍生物來修飾的胜肽,則是最值得注意的。然而其化學修飾物之官能基與訊號強度之間的關係並未探討。本論文將利用開發出新的環化合成方法,來製備出具推電子基、五環、六環、氫氧基及掌性異構之不同功能性之試劑,再與胜肽中離胺酸耦合成一系列的胍基衍生物,經由NMR 鑑定,高效能液相層析儀分析,及LC-MS/MS 確認這些胍基衍生物的形成。利用基質輔助雷射脫附游離質譜,將胰蛋白酶水解之肌紅蛋白中的ㄧ段胜肽與化學試劑耦合之結構與訊號強度之間的探討。經比對結果顯示,六環結構於質譜訊號強化15.1 倍、五環強化9.2 倍、推電子基強化12.3 倍、氫氧基強化7.6 倍與掌性異構強化12.3-12.4 倍。此結果顯示出,電荷的穩定性對訊號靈敏度的提升,具有決定性的影響,對後續研發ICAT 與iTRAQ 等蛋白質定量試劑具有相當重要的指標意義。
    Detection of low abundant proteins is one of challenging topics in proteomics. Guanidino group was demonstrated to enhance the signal instensity in MALDI experiments. This report described a novel synthetic pathway to prepare the cyclic guanidino derivatives. The guanidino moiety was generated by O-ethylisourea and amino group of lysine-specific side chain. The characterization and identification was performed by NMR, HPLC, LC-MS/MS and MALDI. The result suggested the stabilization of positive charge at guanidino group plays an important role in signal enhancement of mass spectra of proteins. These results provide a further application in the ICAT and iTRAQ for
    protein quantification.
    Appears in Collections:[Graduate Institute & Department of Chemistry] Thesis

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